1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68984501, compound

HRID 1467875Notes

Reaction equation

HRID 1467875 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[C:24]([O:28][C:29]([NH:31][CH:32]([CH2:36][C:37]1[CH:38]=[C:39]([CH3:43])[CH:40]=[CH:41][CH:42]=1)[C:33](O)=[O:34])=[O:30])([CH3:27])([CH3:26])[CH3:25].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C.CN(C=O)C>[C:24]([O:28][C:29](=[O:30])[NH:31][CH:32]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[CH:38]=1)[C:33]([N:21]1[CH2:22][CH2:23][CH:18]([N:4]([CH:1]2[CH2:3][CH2:2]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:6])=[O:7])[CH2:19][CH2:20]1)=[O:34])([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamideHCID 27960291-Hydroxybenzotriazole hydrateHCID 43933482-{[(Tert-butoxy)carbonyl]amino}-3-(3-methylphenyl)propanoic acid

Product 1

HCID 68984501HCID 68984501, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-cyclopropyl-N-piperidin-4-yl-3-trifluoromethyl-benzenesulfonamide (400 mg, 1.15 mmol), 2-tert-butoxycarbonylamino-3-m-tolyl-propionic acid (334 mg, 1.2 mmol), 1-hydroxybenzotriazole hydrate (HOBt, 50 mg, 0.37 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 218 mg, 1.15 mmol), and DMF (5 mL) was shaken at room temperature for 8 hours. The reaction mixture was poured into 20 mL of ethyl acetate, washed with 5 mL of 2N HCl solution, saturated NaHCO3 (20 mL), water (10 mL), and brine (10 mL). The organic layer was concentrated under vacuum and purified by column (silica gel, EtOAc/hexane 1/1) to afford the intermediate [2-{4-[cyclopropyl-(3-trifluoromethylbenzenesulfonyl)-amino]piperidin-1-yl}-1-(3-methylbenzyl)-2-oxo-ethyl]carbamic acid tert-butyl ester as colorless oil (600 mg, yield 85%).

Workup

  1. washwashed with 5 mL of 2N HCl solution, saturated NaHCO3 (20 mL), water (10 mL), and brine (10 mL)
  2. concentrationThe organic layer was concentrated under vacuum
  3. custompurified by column (silica gel, EtOAc/hexane 1/1)

Sources & evidence

ORD record
ord-4a09f6a35af04046a05ba9c855cfb9dc
Source dataset
uspto-grants-2015_04
Patent number
US09000174B2

Reaction notes

Loading…